PMCCPMCCPMCC

Search tips
Search criteria 

Advanced


 
Formats
Article sections
Authors
Related links
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1081.
Published online 2010 April 14. doi:  10.1107/S1600536810013012
PMCID: PMC2979274
Copyright © Khan et al. 2010
4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile
F. Nawaz Khan,a P. Manivel,a K. Prabakaran,a Venkatesha R. Hathwar,b and Mehmet Akkurtc*
aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India
bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: akkurt/at/erciyes.edu.tr
Received April 3, 2010; Accepted April 7, 2010.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Small right arrow pointing to: This article has been cited by other articles in PMC.
Abstract
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 π–π inter­actions [centroid–centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical inter­molecular C—H(...)N hydrogen bond.
Related literature
For a related crystal structure, see: Khan et al. (2010 [triangle]).
An external file that holds a picture, illustration, etc. Object name is e-66-o1081-scheme1.jpg Object name is e-66-o1081-scheme1.jpg
Crystal data
  • C23H14N4
  • M r = 346.38
  • Orthorhombic, An external file that holds a picture, illustration, etc. Object name is e-66-o1081-efi1.jpg
  • a = 7.1614 (3) Å
  • b = 18.0957 (7) Å
  • c = 26.4021 (9) Å
  • V = 3421.5 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 290 K
  • 0.25 × 0.21 × 0.17 mm
Data collection
  • Oxford Xcalibur Eos (Nova) CCD detector diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 [triangle]) T min = 0.959, T max = 0.986
  • 14977 measured reflections
  • 3164 independent reflections
  • 1490 reflections with I > 2σ(I)
  • R int = 0.070
Refinement
  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.100
  • S = 0.81
  • 3164 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.20 e Å−3
Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 [triangle]); 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]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013012/rk2199sup1.cif
Click here to view.(21K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013012/rk2199Isup2.hkl
Click here to view.(152K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the FIST program for data collection on the Oxford single-crystal diffractometer at SSCU, IISc, Bangalore. The authors 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.
supplementary crystallographic information
Comment
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).
Experimental
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.
Refinement
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.
Figures
Fig. 1.
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.
Fig. 2.
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.
Crystal data
C23H14N4F(000) = 1440
Mr = 346.38Dx = 1.345 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1235 reflections
a = 7.1614 (3) Åθ = 1.6–20.4°
b = 18.0957 (7) ŵ = 0.08 mm−1
c = 26.4021 (9) ÅT = 290 K
V = 3421.5 (2) Å3Block, colourless
Z = 80.25 × 0.21 × 0.17 mm
Data collection
Oxford Xcalibur Eos (Nova) CCD detector diffractometer3164 independent reflections
Radiation source: Enhance (Mo) X-ray Source1490 reflections with I > 2σ(I)
graphiteRint = 0.070
ω scansθmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)h = −8→7
Tmin = 0.959, Tmax = 0.986k = −21→21
14977 measured reflectionsl = −31→31
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 0.81w = 1/[σ2(Fo2) + (0.0413P)2] where P = (Fo2 + 2Fc2)/3
3164 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
N10.6627 (2)0.33099 (9)0.03366 (6)0.0370 (4)
N20.5820 (3)0.22467 (10)−0.00072 (7)0.0510 (5)
N30.6063 (2)0.27481 (11)−0.03950 (7)0.0495 (5)
N40.5390 (3)0.08980 (15)0.27259 (9)0.0927 (9)
C10.6539 (3)0.33812 (13)−0.01851 (8)0.0395 (5)
C20.6915 (3)0.40722 (12)−0.04237 (8)0.0407 (6)
C30.6888 (3)0.41638 (14)−0.09495 (8)0.0490 (6)
H30.65860.3766−0.11570.059*
C40.7302 (3)0.48368 (15)−0.11611 (9)0.0570 (7)
H40.72970.4894−0.15110.068*
C50.7728 (3)0.54308 (14)−0.08507 (9)0.0581 (7)
H50.80020.5887−0.09960.070*
C60.7754 (3)0.53585 (13)−0.03328 (9)0.0526 (6)
H60.80300.5764−0.01300.063*
C70.7364 (3)0.46741 (12)−0.01110 (8)0.0416 (6)
C80.7527 (3)0.45523 (12)0.04249 (8)0.0454 (6)
H80.78530.49520.06280.054*
C90.7238 (3)0.38972 (12)0.06498 (8)0.0387 (6)
C100.7671 (3)0.37673 (11)0.11909 (8)0.0374 (5)
C110.8907 (3)0.32192 (12)0.13406 (8)0.0456 (6)
H110.94260.29030.11010.055*
C120.9365 (3)0.31454 (14)0.18466 (9)0.0562 (7)
H121.01800.27740.19480.067*
C130.8625 (4)0.36161 (15)0.22007 (9)0.0645 (8)
H130.89350.35610.25410.077*
C140.7438 (4)0.41647 (15)0.20553 (9)0.0595 (7)
H140.69600.44900.22950.071*
C150.6944 (3)0.42380 (13)0.15537 (9)0.0478 (6)
H150.61140.46080.14580.057*
C160.6137 (3)0.25837 (12)0.04252 (8)0.0406 (6)
C170.5906 (3)0.22246 (12)0.09194 (8)0.0403 (5)
C180.6918 (3)0.15870 (13)0.10218 (8)0.0480 (6)
H180.77010.13910.07750.058*
C190.6771 (3)0.12414 (12)0.14857 (9)0.0523 (6)
H190.74740.08210.15540.063*
C200.5575 (3)0.15217 (13)0.18497 (8)0.0480 (6)
C210.4514 (3)0.21414 (13)0.17476 (8)0.0524 (6)
H210.36930.23240.19900.063*
C220.4678 (3)0.24882 (13)0.12834 (8)0.0503 (6)
H220.39570.29030.12140.060*
C230.5459 (3)0.11720 (15)0.23405 (10)0.0629 (8)
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
N10.0393 (10)0.0337 (11)0.0381 (11)−0.0026 (8)−0.0031 (8)−0.0012 (9)
N20.0631 (13)0.0439 (12)0.0459 (12)−0.0068 (10)−0.0062 (10)−0.0041 (11)
N30.0614 (13)0.0457 (13)0.0414 (11)−0.0057 (10)−0.0054 (9)0.0003 (10)
N40.0964 (19)0.124 (2)0.0576 (16)0.0151 (16)0.0099 (14)0.0261 (16)
C10.0394 (14)0.0404 (15)0.0387 (13)−0.0003 (11)−0.0054 (10)−0.0027 (12)
C20.0357 (13)0.0443 (15)0.0421 (14)0.0023 (11)−0.0010 (10)0.0016 (12)
C30.0463 (15)0.0544 (17)0.0463 (15)0.0062 (13)0.0002 (11)0.0032 (13)
C40.0515 (17)0.0687 (19)0.0507 (15)0.0085 (14)0.0028 (12)0.0160 (15)
C50.0464 (16)0.0584 (19)0.0695 (19)−0.0011 (13)−0.0002 (13)0.0241 (15)
C60.0500 (15)0.0465 (16)0.0613 (17)−0.0003 (12)−0.0016 (13)0.0076 (13)
C70.0344 (14)0.0413 (15)0.0490 (14)0.0004 (11)−0.0046 (11)0.0072 (12)
C80.0461 (14)0.0387 (15)0.0513 (15)−0.0011 (11)−0.0052 (12)−0.0054 (12)
C90.0347 (14)0.0368 (15)0.0445 (13)−0.0002 (10)−0.0019 (11)−0.0060 (11)
C100.0399 (14)0.0336 (13)0.0386 (13)−0.0029 (11)−0.0012 (10)−0.0018 (11)
C110.0441 (14)0.0436 (15)0.0492 (15)−0.0011 (12)−0.0005 (11)−0.0047 (12)
C120.0519 (16)0.0604 (18)0.0563 (17)0.0036 (13)−0.0129 (13)0.0072 (15)
C130.075 (2)0.077 (2)0.0416 (15)−0.0091 (16)−0.0111 (14)0.0000 (15)
C140.0721 (18)0.0580 (18)0.0483 (16)−0.0068 (15)0.0073 (14)−0.0115 (14)
C150.0507 (15)0.0429 (15)0.0497 (15)0.0013 (12)0.0008 (12)−0.0051 (13)
C160.0436 (14)0.0361 (14)0.0423 (13)−0.0039 (11)−0.0025 (11)−0.0031 (12)
C170.0400 (13)0.0351 (14)0.0458 (14)−0.0048 (11)−0.0039 (11)−0.0015 (11)
C180.0586 (15)0.0392 (15)0.0463 (15)0.0034 (13)0.0039 (12)−0.0031 (12)
C190.0637 (17)0.0400 (15)0.0532 (16)0.0085 (12)0.0004 (13)0.0023 (13)
C200.0498 (15)0.0497 (16)0.0446 (14)−0.0053 (13)−0.0014 (12)0.0051 (13)
C210.0516 (16)0.0559 (17)0.0497 (16)0.0024 (14)0.0067 (12)−0.0002 (13)
C220.0516 (16)0.0417 (15)0.0575 (16)0.0052 (12)−0.0014 (13)0.0000 (13)
C230.0591 (18)0.075 (2)0.0546 (18)0.0052 (14)0.0030 (14)0.0043 (16)
Geometric parameters (Å, °)
N1—C161.380 (2)C10—C111.387 (3)
N1—C11.385 (2)C11—C121.382 (3)
N1—C91.416 (2)C11—H110.9300
N2—C161.314 (2)C12—C131.371 (3)
N2—N31.379 (2)C12—H120.9300
N3—C11.318 (3)C13—C141.362 (3)
N4—C231.133 (3)C13—H130.9300
C1—C21.426 (3)C14—C151.377 (3)
C2—C31.398 (3)C14—H140.9300
C2—C71.404 (3)C15—H150.9300
C3—C41.372 (3)C16—C171.467 (3)
C3—H30.9300C17—C221.387 (3)
C4—C51.386 (3)C17—C181.389 (3)
C4—H40.9300C18—C191.379 (3)
C5—C61.374 (3)C18—H180.9300
C5—H50.9300C19—C201.384 (3)
C6—C71.398 (3)C19—H190.9300
C6—H60.9300C20—C211.381 (3)
C7—C81.437 (3)C20—C231.445 (3)
C8—C91.342 (3)C21—C221.382 (3)
C8—H80.9300C21—H210.9300
C9—C101.481 (3)C22—H220.9300
C10—C151.384 (3)
C16—N1—C1104.23 (17)C12—C11—H11120.1
C16—N1—C9133.97 (18)C10—C11—H11120.1
C1—N1—C9121.67 (19)C13—C12—C11120.5 (2)
C16—N2—N3108.54 (17)C13—C12—H12119.7
C1—N3—N2107.01 (17)C11—C12—H12119.7
N3—C1—N1110.4 (2)C14—C13—C12120.1 (2)
N3—C1—C2128.7 (2)C14—C13—H13119.9
N1—C1—C2120.8 (2)C12—C13—H13119.9
C3—C2—C7119.7 (2)C13—C14—C15120.1 (2)
C3—C2—C1122.7 (2)C13—C14—H14120.0
C7—C2—C1117.6 (2)C15—C14—H14120.0
C4—C3—C2120.4 (2)C14—C15—C10120.7 (2)
C4—C3—H3119.8C14—C15—H15119.7
C2—C3—H3119.8C10—C15—H15119.7
C3—C4—C5119.7 (2)N2—C16—N1109.78 (18)
C3—C4—H4120.2N2—C16—C17123.23 (19)
C5—C4—H4120.2N1—C16—C17126.94 (19)
C6—C5—C4121.2 (2)C22—C17—C18118.8 (2)
C6—C5—H5119.4C22—C17—C16122.4 (2)
C4—C5—H5119.4C18—C17—C16118.8 (2)
C5—C6—C7119.9 (2)C19—C18—C17120.6 (2)
C5—C6—H6120.0C19—C18—H18119.7
C7—C6—H6120.0C17—C18—H18119.7
C6—C7—C2119.1 (2)C18—C19—C20119.9 (2)
C6—C7—C8122.1 (2)C18—C19—H19120.1
C2—C7—C8118.6 (2)C20—C19—H19120.1
C9—C8—C7124.0 (2)C21—C20—C19120.2 (2)
C9—C8—H8118.0C21—C20—C23119.9 (2)
C7—C8—H8118.0C19—C20—C23119.9 (2)
C8—C9—N1116.90 (19)C20—C21—C22119.7 (2)
C8—C9—C10122.32 (19)C20—C21—H21120.2
N1—C9—C10120.61 (19)C22—C21—H21120.2
C15—C10—C11118.9 (2)C21—C22—C17120.8 (2)
C15—C10—C9119.4 (2)C21—C22—H22119.6
C11—C10—C9121.49 (19)C17—C22—H22119.6
C12—C11—C10119.7 (2)N4—C23—C20179.2 (3)
C16—N2—N3—C10.5 (2)N1—C9—C10—C15−131.8 (2)
N2—N3—C1—N10.3 (2)C8—C9—C10—C11−121.8 (2)
N2—N3—C1—C2−178.9 (2)N1—C9—C10—C1153.2 (3)
C16—N1—C1—N3−0.9 (2)C15—C10—C11—C121.0 (3)
C9—N1—C1—N3175.46 (16)C9—C10—C11—C12176.0 (2)
C16—N1—C1—C2178.40 (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—C151.4 (4)
N1—C1—C2—C3178.35 (17)C13—C14—C15—C10−1.3 (4)
N3—C1—C2—C7178.8 (2)C11—C10—C15—C140.0 (3)
N1—C1—C2—C7−0.4 (3)C9—C10—C15—C14−175.0 (2)
C7—C2—C3—C40.2 (3)N3—N2—C16—N1−1.0 (2)
C1—C2—C3—C4−178.5 (2)N3—N2—C16—C17176.63 (18)
C2—C3—C4—C5−0.8 (3)C1—N1—C16—N21.2 (2)
C3—C4—C5—C60.4 (3)C9—N1—C16—N2−174.51 (19)
C4—C5—C6—C70.7 (3)C1—N1—C16—C17−176.38 (19)
C5—C6—C7—C2−1.2 (3)C9—N1—C16—C177.9 (4)
C5—C6—C7—C8174.57 (19)N2—C16—C17—C22−120.5 (2)
C3—C2—C7—C60.8 (3)N1—C16—C17—C2256.7 (3)
C1—C2—C7—C6179.55 (19)N2—C16—C17—C1857.8 (3)
C3—C2—C7—C8−175.16 (18)N1—C16—C17—C18−125.0 (2)
C1—C2—C7—C83.6 (3)C22—C17—C18—C19−3.0 (3)
C6—C7—C8—C9−177.2 (2)C16—C17—C18—C19178.6 (2)
C2—C7—C8—C9−1.5 (3)C17—C18—C19—C201.4 (3)
C7—C8—C9—N1−3.9 (3)C18—C19—C20—C210.7 (3)
C7—C8—C9—C10171.32 (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—C87.3 (3)C23—C20—C21—C22177.8 (2)
C16—N1—C9—C107.0 (3)C20—C21—C22—C17−0.4 (3)
C1—N1—C9—C10−168.06 (17)C18—C17—C22—C212.5 (3)
C8—C9—C10—C1553.1 (3)C16—C17—C22—C21−179.2 (2)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
C11—H11···N3i0.932.503.418 (3)170
Symmetry codes: (i) x+1/2, −y+1/2, −z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2199).
References
  • 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. [PMC free article] [PubMed]
  • 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. [PubMed]
Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of
International Union of Crystallography