4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile.

In the title mol-ecule, C(23)H(14)N(4), 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, mol-ecules are linked by weak aromatic π-π inter-actions [centroid-centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical inter-molecular C-H⋯N hydrogen bond.

Related literature

For a related crystal structure, see: Khan et al. (2010 ▶).

Experimental

Crystal data

C23H14N4

M = 346.38

Orthorhombic,

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 ▶) 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 ▶); cell refinement: CrysAlis PRO CCD; 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013012/rk2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013012/rk2199Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N3i	0.93	2.50	3.418 (3)	170

Symmetry code: (i) .