3-(4-Chloro-phen-yl)-5-phenyl-1,2,4-triazolo[3,4-a]isoquinoline.

In the title mol-ecule, C(22)H(14)ClN(3), 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 mol-ecule is stabilized by a weak intra-molecular π-π inter-action [centroid-centroid distance = 3.7089 (10) Å] between the benzene and phenyl rings. In the crystal structure, weak inter-molecular C-H⋯N hydrogen bonds and C-H⋯π inter-actions link the mol-ecules.

Related literature

For the synthesis and anti­helmintic activity of triazolo compounds similar to the title compound, see: Nadkarni et al. (2001 ▶); Hui et al. (1999 ▶). For related structures, see: Khan et al. (2010 ▶); Zou et al. (2004 ▶).

Experimental

Crystal data

C22H14ClN3

M = 355.81

Monoclinic,

a = 7.9841 (3) Å

b = 9.0679 (4) Å

c = 23.9881 (11) Å

β = 93.078 (4)°

V = 1734.20 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 290 K

0.40 × 0.32 × 0.25 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.902, T max = 0.945

19413 measured reflections

3216 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 0.97

3216 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.21 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/S1600536810013668/bg2341sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013668/bg2341Isup2.hkl

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

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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) .