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

In the title mol-ecule, C(21)H(15)ClN(4)S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.054 (2) Å and a maximum deviation of 0.098 (2) Å from the mean plane for the triazole ring C atom that is bonded to the thia-zole ring. The thia-zole and benzene rings are twisted by 66.36 (7) and 56.32 (7)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯N inter-actions along the a axis. The mol-ecular conformation is stabilized by a weak intra-molecular π-π inter-action involving the thia-zole and benzene rings, with a centroid-centroid distance of 3.6546 (11) Å. In addition, two other intermolecular π-π stacking inter-actions are observed, between the triazole and benzene rings and between the dihydro-pyridine and benzene rings [centroid-centroid distances = 3.6489 (11) and 3.5967 (10) Å, respectively].

Related literature

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

Experimental

Crystal data

C21H15ClN4S

M = 390.89

Triclinic,

a = 7.8286 (5) Å

b = 8.1754 (6) Å

c = 15.1264 (9) Å

α = 93.514 (5)°

β = 94.805 (5)°

γ = 105.963 (6)°

V = 923.92 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 290 K

0.40 × 0.25 × 0.24 mm

Data collection

Oxford Xcalibur diffractometer with an Eos (Nova) CCD detector

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.851, T max = 0.924

19579 measured reflections

3439 independent reflections

2518 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.111

S = 1.09

3439 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.20 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/S160053681001278X/fj2293sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001278X/fj2293Isup2.hkl

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

C21H15ClN4S	Z = 2
Mr = 390.89	F(000) = 404
Triclinic, P1	Dx = 1.405 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8286 (5) Å	Cell parameters from 954 reflections
b = 8.1754 (6) Å	θ = 2.0–20.4°
c = 15.1264 (9) Å	µ = 0.33 mm−1
α = 93.514 (5)°	T = 290 K
β = 94.805 (5)°	Block, pale yellow
γ = 105.963 (6)°	0.40 × 0.25 × 0.24 mm
V = 923.92 (11) Å3

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	3439 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2518 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.851, Tmax = 0.924	k = −9→9
19579 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0635P)2] where P = (Fo2 + 2Fc2)/3
3439 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.20 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
S1	0.55766 (7)	0.44377 (7)	0.27355 (3)	0.05951 (19)
Cl1	0.90834 (9)	0.16939 (8)	0.06573 (5)	0.0843 (2)
N1	0.84486 (17)	0.86756 (18)	0.31082 (9)	0.0404 (3)
N2	0.69901 (19)	1.0456 (2)	0.36035 (10)	0.0527 (4)
N3	0.57837 (19)	0.9079 (2)	0.31201 (11)	0.0552 (4)
N4	0.4093 (2)	0.4452 (2)	0.11718 (11)	0.0566 (4)
C1	0.8562 (2)	1.0182 (2)	0.36077 (11)	0.0422 (4)
C2	1.0238 (2)	1.1181 (2)	0.40777 (11)	0.0424 (4)
C3	1.0384 (3)	1.2657 (2)	0.46264 (12)	0.0518 (5)
H3	0.9390	1.3053	0.4684	0.062*
C4	1.2006 (3)	1.3523 (2)	0.50822 (13)	0.0567 (5)
H4	1.2103	1.4503	0.5452	0.068*
C5	1.3493 (3)	1.2952 (3)	0.49973 (13)	0.0572 (5)
H5	1.4581	1.3545	0.5313	0.069*
C6	1.3375 (2)	1.1514 (3)	0.44506 (13)	0.0542 (5)
H6	1.4388	1.1150	0.4390	0.065*
C7	1.1733 (2)	1.0589 (2)	0.39819 (11)	0.0444 (4)
C8	1.1543 (2)	0.9065 (2)	0.34138 (12)	0.0466 (4)
H8	1.2558	0.8710	0.3341	0.056*
C9	0.9971 (2)	0.8117 (2)	0.29783 (11)	0.0423 (4)
C10	0.9794 (2)	0.6564 (2)	0.23864 (11)	0.0428 (4)
C11	1.0353 (2)	0.5235 (3)	0.27137 (13)	0.0519 (5)
H11	1.0870	0.5347	0.3299	0.062*
C12	1.0157 (3)	0.3744 (3)	0.21852 (14)	0.0573 (5)
H12	1.0532	0.2853	0.2412	0.069*
C13	0.9398 (3)	0.3592 (3)	0.13168 (13)	0.0541 (5)
C14	0.8902 (2)	0.4919 (3)	0.09643 (12)	0.0527 (5)
H14	0.8433	0.4820	0.0371	0.063*
C15	0.9105 (2)	0.6405 (2)	0.14989 (12)	0.0475 (4)
H15	0.8776	0.7311	0.1262	0.057*
C16	0.6634 (2)	0.8009 (2)	0.28300 (11)	0.0453 (4)
C17	0.5732 (2)	0.6376 (2)	0.23238 (12)	0.0471 (4)
C18	0.4858 (2)	0.6136 (2)	0.14858 (12)	0.0498 (5)
C19	0.4738 (3)	0.7494 (3)	0.09026 (15)	0.0764 (7)
H19A	0.3563	0.7645	0.0884	0.115*
H19B	0.4969	0.7176	0.0312	0.115*
H19C	0.5605	0.8544	0.1132	0.115*
C20	0.4383 (2)	0.3425 (3)	0.17513 (14)	0.0558 (5)
C21	0.3769 (4)	0.1526 (3)	0.16023 (18)	0.0799 (7)
H21A	0.2505	0.1137	0.1641	0.120*
H21B	0.4382	0.1043	0.2048	0.120*
H21C	0.4023	0.1173	0.1023	0.120*

	U11	U22	U33	U12	U13	U23
S1	0.0593 (3)	0.0633 (4)	0.0552 (3)	0.0153 (3)	0.0034 (2)	0.0122 (2)
Cl1	0.0961 (5)	0.0658 (4)	0.0907 (5)	0.0316 (3)	−0.0026 (3)	−0.0189 (3)
N1	0.0364 (8)	0.0490 (9)	0.0405 (8)	0.0185 (7)	0.0070 (6)	0.0052 (6)
N2	0.0451 (9)	0.0614 (10)	0.0577 (10)	0.0276 (8)	0.0029 (7)	−0.0021 (8)
N3	0.0402 (9)	0.0680 (11)	0.0614 (10)	0.0249 (8)	0.0008 (7)	−0.0027 (8)
N4	0.0550 (10)	0.0589 (11)	0.0559 (10)	0.0203 (9)	−0.0029 (8)	−0.0027 (8)
C1	0.0411 (10)	0.0502 (10)	0.0406 (9)	0.0200 (8)	0.0084 (7)	0.0062 (8)
C2	0.0439 (10)	0.0467 (10)	0.0384 (9)	0.0135 (8)	0.0085 (7)	0.0095 (8)
C3	0.0581 (12)	0.0523 (11)	0.0503 (11)	0.0232 (10)	0.0079 (9)	0.0074 (9)
C4	0.0691 (13)	0.0485 (11)	0.0486 (11)	0.0115 (10)	0.0044 (9)	0.0009 (9)
C5	0.0509 (12)	0.0561 (13)	0.0566 (12)	0.0024 (10)	0.0006 (9)	0.0088 (10)
C6	0.0384 (10)	0.0640 (13)	0.0588 (12)	0.0106 (9)	0.0084 (8)	0.0072 (10)
C7	0.0399 (10)	0.0520 (11)	0.0435 (10)	0.0135 (8)	0.0111 (7)	0.0098 (8)
C8	0.0342 (9)	0.0601 (12)	0.0501 (10)	0.0192 (9)	0.0110 (8)	0.0049 (9)
C9	0.0364 (9)	0.0548 (11)	0.0422 (9)	0.0209 (8)	0.0116 (7)	0.0083 (8)
C10	0.0362 (9)	0.0540 (11)	0.0435 (10)	0.0190 (8)	0.0112 (7)	0.0054 (8)
C11	0.0526 (11)	0.0644 (13)	0.0468 (11)	0.0290 (10)	0.0064 (8)	0.0078 (9)
C12	0.0618 (12)	0.0573 (12)	0.0628 (13)	0.0308 (11)	0.0119 (10)	0.0114 (10)
C13	0.0511 (11)	0.0549 (12)	0.0586 (12)	0.0183 (10)	0.0109 (9)	−0.0014 (9)
C14	0.0518 (11)	0.0665 (13)	0.0436 (10)	0.0232 (10)	0.0066 (8)	0.0011 (9)
C15	0.0457 (10)	0.0586 (12)	0.0454 (10)	0.0242 (9)	0.0099 (8)	0.0085 (9)
C16	0.0344 (9)	0.0608 (12)	0.0442 (10)	0.0189 (9)	0.0041 (7)	0.0053 (9)
C17	0.0354 (9)	0.0592 (12)	0.0495 (11)	0.0181 (9)	0.0048 (8)	0.0037 (9)
C18	0.0460 (10)	0.0538 (11)	0.0521 (11)	0.0215 (9)	−0.0021 (8)	−0.0002 (9)
C19	0.0994 (17)	0.0625 (14)	0.0660 (14)	0.0318 (13)	−0.0244 (12)	0.0001 (11)
C20	0.0501 (11)	0.0564 (12)	0.0623 (13)	0.0169 (10)	0.0088 (9)	0.0039 (10)
C21	0.0942 (18)	0.0585 (14)	0.0864 (17)	0.0212 (13)	0.0081 (13)	0.0040 (12)

S1—C17	1.7150 (19)	C8—C9	1.351 (2)
S1—C20	1.722 (2)	C8—H8	0.9300
Cl1—C13	1.7387 (19)	C9—C10	1.475 (2)
N1—C1	1.382 (2)	C10—C11	1.382 (2)
N1—C16	1.392 (2)	C10—C15	1.389 (2)
N1—C9	1.413 (2)	C11—C12	1.381 (3)
N2—C1	1.310 (2)	C11—H11	0.9300
N2—N3	1.376 (2)	C12—C13	1.379 (3)
N3—C16	1.313 (2)	C12—H12	0.9300
N4—C20	1.299 (3)	C13—C14	1.371 (3)
N4—C18	1.378 (2)	C14—C15	1.381 (2)
C1—C2	1.441 (2)	C14—H14	0.9300
C2—C3	1.394 (2)	C15—H15	0.9300
C2—C7	1.399 (2)	C16—C17	1.460 (2)
C3—C4	1.374 (3)	C17—C18	1.365 (3)
C3—H3	0.9300	C18—C19	1.477 (3)
C4—C5	1.380 (3)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C5—C6	1.372 (2)	C19—H19C	0.9600
C5—H5	0.9300	C20—C21	1.490 (3)
C6—C7	1.405 (3)	C21—H21A	0.9600
C6—H6	0.9300	C21—H21B	0.9600
C7—C8	1.435 (2)	C21—H21C	0.9600
C17—S1—C20	89.71 (9)	C12—C11—H11	119.5
C1—N1—C16	104.18 (13)	C10—C11—H11	119.5
C1—N1—C9	122.02 (14)	C13—C12—C11	119.11 (18)
C16—N1—C9	133.80 (15)	C13—C12—H12	120.4
C1—N2—N3	106.96 (14)	C11—C12—H12	120.4
C16—N3—N2	109.14 (14)	C14—C13—C12	121.03 (18)
C20—N4—C18	111.44 (17)	C14—C13—Cl1	119.56 (16)
N2—C1—N1	110.74 (15)	C12—C13—Cl1	119.41 (16)
N2—C1—C2	128.52 (16)	C13—C14—C15	119.30 (18)
N1—C1—C2	120.68 (14)	C13—C14—H14	120.3
C3—C2—C7	120.43 (17)	C15—C14—H14	120.3
C3—C2—C1	122.28 (16)	C14—C15—C10	120.84 (18)
C7—C2—C1	117.26 (16)	C14—C15—H15	119.6
C4—C3—C2	119.62 (18)	C10—C15—H15	119.6
C4—C3—H3	120.2	N3—C16—N1	108.91 (16)
C2—C3—H3	120.2	N3—C16—C17	123.14 (15)
C3—C4—C5	120.64 (19)	N1—C16—C17	127.92 (15)
C3—C4—H4	119.7	C18—C17—C16	126.79 (17)
C5—C4—H4	119.7	C18—C17—S1	109.80 (14)
C6—C5—C4	120.41 (19)	C16—C17—S1	123.38 (14)
C6—C5—H5	119.8	C17—C18—N4	114.72 (17)
C4—C5—H5	119.8	C17—C18—C19	125.94 (18)
C5—C6—C7	120.40 (18)	N4—C18—C19	119.29 (17)
C5—C6—H6	119.8	C18—C19—H19A	109.5
C7—C6—H6	119.8	C18—C19—H19B	109.5
C2—C7—C6	118.48 (17)	H19A—C19—H19B	109.5
C2—C7—C8	119.24 (16)	C18—C19—H19C	109.5
C6—C7—C8	122.28 (16)	H19A—C19—H19C	109.5
C9—C8—C7	123.62 (16)	H19B—C19—H19C	109.5
C9—C8—H8	118.2	N4—C20—C21	124.4 (2)
C7—C8—H8	118.2	N4—C20—S1	114.31 (16)
C8—C9—N1	116.99 (16)	C21—C20—S1	121.26 (17)
C8—C9—C10	123.21 (15)	C20—C21—H21A	109.5
N1—C9—C10	119.80 (14)	C20—C21—H21B	109.5
C11—C10—C15	118.60 (17)	H21A—C21—H21B	109.5
C11—C10—C9	119.53 (16)	C20—C21—H21C	109.5
C15—C10—C9	121.87 (16)	H21A—C21—H21C	109.5
C12—C11—C10	121.00 (18)	H21B—C21—H21C	109.5
C1—N2—N3—C16	−0.8 (2)	N1—C9—C10—C15	57.7 (2)
N3—N2—C1—N1	2.2 (2)	C15—C10—C11—C12	−3.1 (3)
N3—N2—C1—C2	−174.89 (17)	C9—C10—C11—C12	178.05 (16)
C16—N1—C1—N2	−2.68 (19)	C10—C11—C12—C13	0.3 (3)
C9—N1—C1—N2	177.60 (14)	C11—C12—C13—C14	2.5 (3)
C16—N1—C1—C2	174.71 (15)	C11—C12—C13—Cl1	−178.02 (15)
C9—N1—C1—C2	−5.0 (2)	C12—C13—C14—C15	−2.5 (3)
N2—C1—C2—C3	0.4 (3)	Cl1—C13—C14—C15	178.05 (13)
N1—C1—C2—C3	−176.44 (16)	C13—C14—C15—C10	−0.4 (3)
N2—C1—C2—C7	178.86 (17)	C11—C10—C15—C14	3.1 (3)
N1—C1—C2—C7	2.0 (2)	C9—C10—C15—C14	−178.05 (15)
C7—C2—C3—C4	−0.7 (3)	N2—N3—C16—N1	−0.8 (2)
C1—C2—C3—C4	177.71 (16)	N2—N3—C16—C17	177.39 (16)
C2—C3—C4—C5	0.4 (3)	C1—N1—C16—N3	2.09 (18)
C3—C4—C5—C6	0.4 (3)	C9—N1—C16—N3	−178.24 (17)
C4—C5—C6—C7	−1.1 (3)	C1—N1—C16—C17	−176.03 (17)
C3—C2—C7—C6	0.1 (3)	C9—N1—C16—C17	3.6 (3)
C1—C2—C7—C6	−178.40 (15)	N3—C16—C17—C18	66.9 (3)
C3—C2—C7—C8	179.91 (16)	N1—C16—C17—C18	−115.2 (2)
C1—C2—C7—C8	1.4 (2)	N3—C16—C17—S1	−111.10 (18)
C5—C6—C7—C2	0.8 (3)	N1—C16—C17—S1	66.8 (2)
C5—C6—C7—C8	−179.03 (17)	C20—S1—C17—C18	1.01 (14)
C2—C7—C8—C9	−2.1 (3)	C20—S1—C17—C16	179.31 (15)
C6—C7—C8—C9	177.69 (17)	C16—C17—C18—N4	−178.77 (15)
C7—C8—C9—N1	−0.7 (3)	S1—C17—C18—N4	−0.5 (2)
C7—C8—C9—C10	179.18 (16)	C16—C17—C18—C19	3.7 (3)
C1—N1—C9—C8	4.3 (2)	S1—C17—C18—C19	−178.11 (17)
C16—N1—C9—C8	−175.35 (17)	C20—N4—C18—C17	−0.5 (2)
C1—N1—C9—C10	−175.59 (15)	C20—N4—C18—C19	177.28 (18)
C16—N1—C9—C10	4.8 (3)	C18—N4—C20—C21	−178.43 (18)
C8—C9—C10—C11	56.7 (2)	C18—N4—C20—S1	1.3 (2)
N1—C9—C10—C11	−123.46 (18)	C17—S1—C20—N4	−1.35 (15)
C8—C9—C10—C15	−122.2 (2)	C17—S1—C20—C21	178.36 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N2i	0.93	2.62	3.495 (2)	158
C8—H8···N3i	0.93	2.51	3.383 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N2i	0.93	2.62	3.495 (2)	158
C8—H8⋯N3i	0.93	2.51	3.383 (2)	156

Symmetry code: (i) .